US6060582A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Photopolymerizable biodegradable hydrogels as tissue contacting materials and controlled-release carriers
Assignee: The University of Texas System
•
Filing: 1998-08-04
•
Granted: 2000-05-09
•
Expires: 2018-08-04
Abstract
Abstract Hydrogels of polymerized and crosslinked macromers comprising hydrophilic oligomers having biodegradable monomeric or oligomeric extensions, which biodegradable extensions are terminated on free ends with end cap monomers or oligomers capable of polymerization and cross linking are described. The hydrophilic core itself may be degradable, thus combining the core and extension functions. Macromers are polymerized using free radical initiators under the influence of long wavelength ultraviolet light, visible light excitation or thermal energy. Biodegradation occurs at the linkages within the extension oligomers and results in fragments which are non-toxic and easily removed from the body. Preferred applications for the hydrogels include prevention of adhesion formation after surgical procedures, controlled release of drugs and other bioactive species, temporary protection or separation of tissue surfaces, adhering of sealing tissues together, and preventing the attachment of cells to tissue surfaces.
Inventors
- 👤 Jeffrey A. Hubbell
- 👤 Chandrashekhar P. Pathak
- 👤 Amarpreet S. Sawhney
- 👤 Neil P. Desai
- 👤 Jennifer L. Hill-West
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 08:05
CPC Classifications
A; A61; A61K; A61K9/00; A61K9/48; A61K9/50; A61K9/0012; A61K9/0019; A61K9/0024; A61K38/00; A61K38/16; A61K38/43; A61K38/46; A61K38/47; A61K38/48; A61K38/49; A61K47/00; A61K47/30; A61K47/32; A61K9/14; A61K9/16; A61K9/1605; A61K9/1629; A61K9/1635; A61K9/1641; A61K9/1647; A61L; A61L24/00; A61L24/001; A61L24/0031; A61L24/0042; A61L24/04; A61L24/046; A61L26/00; A61L26/0009; A61L26/0019; A61L27/00; A61L27/28; A61L27/34; A61L27/36; A61L27/38; A61L27/3839; A61L27/50; A61L27/52; A61L29/00; A61L29/08; A61L29/085; A61L31/00; A61L31/08; A61L31/10; A61L31/14; A61L31/145; A61L31/148; A61L31/16; C; C08; C08F; C08F290/00; C08F290/02; C08F290/06; C08F291/00; C09; C09D; C09D153/00; C09J; C09J153/00; C12; C12N; C12N11/00; C12N11/02; C12N11/04; C12N5/00; C12N5/0012; C12N5/06; C12N5/0602; C12N5/0676; C12N5/0677; C12Y; C12Y302/00; C12Y302/01; C12Y302/01017; C12Y304/00; C12Y304/21; C12Y304/21068; A61K35/00; A61K35/12; A61K2035/126; A61K2035/128; A61L2300/00; A61L2300/40; A61L2300/424; A61L2300/60; A61L2300/602; B; B82; B82Y; B82Y5/00; C12N2533/00; C12N2533/30; C12N2533/32; C12N2533/40; C12N2533/70; C12N2533/74; Y; Y10; Y10T; Y10T428/00; Y10T428/29; Y10T428/2913; Y10T428/2933; Y10T428/2964; Y10T428/2967; Y10T428/31504; Y10T428/31786
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
139 words
A biodegradable, photopolymerizable, and at least substantially water soluble macromer comprising: components P, B, and L, wherein P comprises an organic group capable of being crosslinked by photopolymerization, L is a linking group, comprising at least one repeating unit, and L exhibits water solubility or biodegradability, and B is a backbone group, comprising at least one repeating unit, and B exhibits water solubility or biodegradability; wherein each P is separated by at least one biodegradable group from any other P; wherein at least one of B and L is biodegradable; wherein at least one of the repeating units of B and L are different; wherein the macromer as a whole is substantially water soluble; wherein there are at least two P groups per molecule; and wherein a plurality of P groups are linked to B groups via L groups.
Claim 2
Dependent Claim
139 words
A biodegradable, photopolymerizable, and at least substantially water soluble macromer comprising: components P, B, and L, wherein P comprises an organic group capable of being crosslinked by photopolymerization, L is a linking group, comprising at least one repeating unit, and L exhibits water solubility or biodegradability, and B is a backbone group, comprising at least one repeating unit, and B exhibits water solubility or biodegradability; wherein each P is separated by at least one biodegradable group from any other P; wherein at least one of B and L is biodegradable; wherein at least one of the repeating units of B and L are different; wherein the macromer as a whole is substantially water soluble; wherein there are at least two P groups per molecule; and wherein a plurality of P groups are linked to B groups via L groups.
Claim 3
Dependent Claim
20 words
The macromer of claim 1, wherein substantially all of the P groups are linked to B groups via L groups.
Claim 4
Dependent Claim
23 words
The macromer of claim 1, wherein B comprises poly(ethylene glycol), L comprises biodegradable poly(α-hydroxy acid), and P comprises an acrylate oligomer or monomer.
Claim 5
Dependent Claim
49 words
The macromer of claim 3 wherein the poly(ethylene glycol) has a molecular weight between about 400 and 30,000 Da, the poly(α-hydroxy acid) oligomers have a molecular weight between about 200 and 1200 Da, and the acrylate oligomers or monomers have a molecular weight between about 50 and 200 Da.
Claim 6
Dependent Claim
42 words
The macromer of claim 3 wherein the poly(ethylene glycol) has a molecular weight of about 10,000 Da, the poly(glycolic acid) oligomers have a molecular weight about 250 Da, and the acrylate oligomers or monomers have a molecular weight of about 100 Da.
Claim 7
Dependent Claim
18 words
The macromer of claim 1 wherein P comprises a carbon-carbon double bond capable of crosslinking and polymerizing macromers.
Claim 8
Dependent Claim
32 words
The macromer of claim 1 wherein crosslinking and polymerization of the macromer are initiated by a light-sensitive free-radical polymerization initiator with or without a cocatalyst, further comprising a free radical polymerization initiator.
Claim 9
Dependent Claim
21 words
The macromer of claim 1 wherein L is selected from the group consisting of poly(α-hydroxy acids), poly(lactones), poly(anhydrides), poly(orthoesters), and poly(phosphoesters).
Claim 10
Dependent Claim
32 words
The macromer of claim 1 wherein B is selected from the group consisting of poly(ethylene glycol), poly(ethylene oxide), poly(vinyl alcohol), poly(vinylpyrrolidone), poly(ethyloxazoline), poly(ethylene oxide)-co-poly(propyleneoxide) block copolymers, polysaccharides, carbohydrates, proteins, and combinations thereof.
Claim 11
Dependent Claim
161 words
A biodegradable, photopolymerizable, and at least substantially water soluble macromer having the formula (P m L n ) q wherein: P comprises an organic group capable of being crosslinked by photopolymerization, L comprises a linking group covalently attached to P, comprising at least one repeating unit, and L exhibits water solubility or biodegradability, and B comprises a backbone group covalently attached to L, comprising at least one repeating unit, and B exhibits water solubility or biodegradability; wherein n is a positive integer, m is at least one, and q is at least one; wherein each P is separated by at least one biodegradable group from any other P; wherein at least one of B and L is biodegradable; wherein at least one of the repeating units of B and L are different; wherein the macromer as a whole is substantially water soluble; and wherein the average number of P groups per B groups in the macromer is at least about 1.5.
Claim 12
Dependent Claim
161 words
A biodegradable, photopolymerizable, and at least substantially water soluble macromer having the formula (P m L n ) q wherein: P comprises an organic group capable of being crosslinked by photopolymerization, L comprises a linking group covalently attached to P, comprising at least one repeating unit, and L exhibits water solubility or biodegradability, and B comprises a backbone group covalently attached to L, comprising at least one repeating unit, and B exhibits water solubility or biodegradability; wherein n is a positive integer, m is at least one, and q is at least one; wherein each P is separated by at least one biodegradable group from any other P; wherein at least one of B and L is biodegradable; wherein at least one of the repeating units of B and L are different; wherein the macromer as a whole is substantially water soluble; and wherein the average number of P groups per B groups in the macromer is at least about 1.5.
Claim 13
Dependent Claim
23 words
The macromer of claim 10, wherein B comprises poly(ethylene glycol), L comprises biodegradable poly(α-hydroxy acid), and P comprises an acrylate oligomer or monomer.
Claim 14
Dependent Claim
49 words
The macromer of claim 11 wherein the poly(ethylene glycol) has a molecular weight between about 400 and 30,000 Da, the poly(α-hydroxy acid) oligomers have a molecular weight between about 200 and 1200 Da, and the acrylate oligomers or monomers have a molecular weight between about 50 and 200 Da.
Claim 15
Dependent Claim
42 words
The macromer of claim 11 wherein the poly(ethylene glycol) has a molecular weight of about 10,000 Da, the poly(glycolic acid) oligomers have a molecular weight about 250 Da, and the acrylate oligomers or monomers have a molecular weight of about 100 Da.
Claim 16
Dependent Claim
18 words
The macromer of claim 10 wherein P comprises a carbon-carbon double bond capable of crosslinking and polymerizing macromers.
Claim 17
Dependent Claim
32 words
The macromer of claim 10 wherein crosslinking and polymerization of the macromer are initiated by a light-sensitive free-radical polymerization initiator with or without a cocatalyst, further comprising a free radical polymerization initiator.
Claim 18
Dependent Claim
21 words
The macromer of claim 10 wherein L is selected from the group consisting of poly(α-hydroxy acids), poly(lactones), poly(anhydrides), poly(orthoesters), and poly(phosphoesters).
Claim 19
Dependent Claim
32 words
The macromer of claim 10 wherein B is selected from the group consisting of poly(ethylene glycol), poly(ethylene oxide), poly(vinyl alcohol), poly(vinylpyrrolidone), poly(ethyloxazoline), poly(ethylene oxide)-co-poly(propyleneoxide) block copolymers, polysaccharides, carbohydrates, proteins, and combinations thereof.
References Cited (Backward Citations)
US3640741A
Cited
DE2232839A1
Cited
US3960150A
Cited
US3981303A
Cited
US3986510A
Cited
US3993071A
Cited
US3925895A
Cited
US4450150A
Cited
US4193845A
Cited
US4080969A
Cited
US4194066A
Cited
US4076800A
Cited
US4226938A
Cited
US4195129A
Cited
US4272617A
Cited
US4118470A
Cited
US4095600A
Cited
US4298839A
Cited
JPS5589314A
Cited
US4310397A
Cited
US4295762A
Cited
US4352883A
Cited
US4391909A
Cited
US4409331A
Cited
JPS5611916A
Cited
JPS5622306A
Cited
US4298002A
Cited
US4376839A
Cited
JPS56151701A
Cited
US4475160A
Cited
US4434150A
Cited
US4512910A
Cited
US4942035A
Cited
US4526938A
Cited
US4452973A
Cited
US4689293A
Cited
US4806355A
Cited
US4533445A
Cited
US4631188A
Cited
US4511478A
Cited
US4605622A
Cited
US4655777A
Cited
US4563489A
Cited
US4663286A
Cited
US4749620A
Cited
US4744933A
Cited
US4774178A
Cited
US4650488A
Cited
US4636552A
Cited
US4637931A
Cited
EP0195304A2
Cited
US4950596A
Cited
US4741337A
Cited
US4808399A
Cited
US4889722A
Cited
US5061281A
Cited
US4741872A
Cited
US4744365A
Cited
US4716203A
Cited
US4957744A
Cited
US4913903A
Cited
JPS63199208A
Cited
US4933430A
Cited
DE3716544A1
Cited
US4826945A
Cited
US4804691A
Cited
US4912934A
Cited
US5129889A
Cited
US4923645A
Cited
US4916193A
Cited
US5185408A
Cited
US4891263A
Cited
US5120802A
Cited
US4888413A
Cited
EP0354855A2
Cited
US4925677A
Cited
US4938763A
Cited
US4938763B1
Cited
US5278202A
Cited
US5278201A
Cited
US5135751A
Cited
US5324775A
Cited
DD277454A1
Cited
US5258034A
Cited
US4999417A
Cited
US5108755A
Cited
EP0399441A2
Cited
US4994277A
Cited
US5219564A
Cited
EP0466648A1
Cited
US5627233A
Cited
US5410016A
Cited
US5206303A
Cited
US5153002A
Cited
EP0539751A1
Cited
US5318780A
Cited
US5270400A
Cited
US5417983A
Cited
US5626863A
Cited
US5731406A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2003-05-09 | 2003-11-08 | 2004-05-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2007-05-09 | 2007-11-08 | 2008-05-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2011-05-09 | 2011-11-08 | 2012-05-09 | $7700.00 | Window Closed / Lapsed |